Azo dyestuffs



the methods described in (1904); Berichte 39, 2439 parts of 25% cloth was padded with Patented Apr. 17, 1945 cf)- Joseph to E. mington,

No Drawing.

*AzonYEs'rUFrs v ,v ,r h H. Trepagnier, Wilmington,Del., assignor I. du Pont 'de Nemours & Company, DeL, a corporation of Delaware pplication Junei'z, 343, I

Serial No. 491,2215 o: 8 Claims. (01. 260 -155) shades, and which have good fastnes 's, particularly to light and chlorine. y p

The objects of the invention are accomplished, generally speaking," by coupling a diazotize'd-primary arylamine free from water" solubilizing groups such as carboxylic and sul'for' ic acidii'to anhydroxy-benz-(a) -acridine, in which the hydroxy group is more of positions 2, 9, and-10. The fb'enz-(a) -acridine"nuc1'e'usmay also contain halogen substituents, of ferred member. Y

The new dyestuffs may be produced on the fiber by impregnating the fiber with an alkaline solution of the coupling component, followed by development with a diazotiz ed arylamine free from water solubili'zing groups. The'dyestuffs can also be efficiently produced by stabilizing the diazo in alkaline medium with a compound such as 2- ethyl-amino--sulfo-benzoicacid, incorporating it with the coupling component in a printing paste, applying the paste to thefiber and developing by steam or acidifiedsteam. I

The coupling components maybe prepared by Berichte 3'7, 3080 (-1906), and German Patent 123,260.

Diazotization of the diazo component may be carried out in the usual manner.

The following examples illustrate but do not limit the invention: 1

EXAMPLE I Twenty parts of 2-hydroxy-benz-(a)-acridine were dissolved in a mixture of 40 parts of alcohol, 13 parts of a 25% caustic soda solution and30 parts of warm water. This was diluted to 1,000 parts by volume by adding a warm solutionof 13 caustic soda solution and 2,,parts 1,000 parts of water. Cotton this solution and, after dyeing, developed with a properly buffered solution of diazotized 5-nitro-2-amino-anis0le. After soaping, a beautiful chocolate brown shade was of Alkanol B in .15 n which chlorine is a preproduced, which was fast to light and chlorine; The structure of the dye is probably: i

V s H 7 Using thesame coupling components and varying, the, diazo component, the following wide range of'shades was obtained: .Table I Diazocomponent Shade 2,5'diclilo ro-anilinen Redbrown. Dianisidiue Blue black. 4-nitro-2-amino-anisole Chocolate brown." l-amino anthraquinone Very dull red. i-chloro-z-nitro-aniline Chocolate brown; B-chloro-aniline; Bed'brown. 4-nitro-an' e Brown. 2 nitro-aniline Red brown; 3-nitro-4-amino-anisole Chocolate brown." 5-nitro-2-amino-toluene Do.

Emmi-r. II I Cotton broadcloth was printed with a printing paste containing in 1,000 gram:

' Grams Z-hydroxy-benz-(a) -acridine 16 The diazoimino compound prepared from difor four minutes and acetic acid,

The printwas dried, steamed in steam containing formic.

soaped in a F. soa solution, rinsed and dried.

A rich chocolate brown was obtained which had EXAMPLE III Cotton sheeting was padded with an alkaline solution of 2-hydroxy-ll-chloro-benz-(a) -acridine at a concentration of 20 parts per thousand. The material was dried and pieces of it were developed with the diazotized amines listed in Table II which also lists the colors obtained.

Table II Diezo component 5 g f Dianisid inp Blue black.

5-nitro-2-amino-anisole 4-n1tro-2-ammo-an1sole.

Very dull violet. Red brown.

3-chloro-aniline Do. l-amino-anthraquinone Do. 5-nitro -2-amino-toluene Chocolate-brown. 4-chloro-2-nitro-aniline Brown. 2,5-dichloro-aniline; Red-brown EXAMPLE IV Cotton sheeting was padded with a solution containing 15 parts per thousand of 9-hydroxy benz'-(a)-acridine. By developing pieces of this padded cloth with the diazo components indicated in Table III the colors. described in the table were produced.

Table III Diazo component g f gg l-amino-anthraquinone Scarlet. 5-nitro-2-amino-anisole Do.

-chloro-2-amino-anis0le. Orange. 5-nitro-2-a1nino-t0luene. Scarlet. Dianisidine Dullredblue.

EXAMPLE: V

Substituting the diazo components of Table IV for those of Table III and l0-hydroxy-benz (a) acridine for th 9-hydroxy-benz-(a) -acridine in Example IV, the shades indicated in Table, IV were obtained. ltl-hydroxy-benzJa) -acridine was prepared by hydrolyzing IO-acetyl-aminobenz-(a)-acridine with 10% sulfuric acid1at-200i C. in a. manner very similar to that used in preparing Q-hydroxy-benz-(a) -acridine.-

Table IV Shade oi soaped Diazo component dyeing 4-nitro-2-amino-anisole 5-nitro-2-amino-an isole l-ammo-anthraqumone.

ed. 'Yellow scarlet.

wherein, R is an. aromatic radical, free from. solubilizing groups of the class consisting of the benzene, biphenyl and anthraquinoneseries and OH is in one of the positions 2, 9 and 10.

2. A. compound. represented by the formula of claim. 1 in which R is, a. radical of the benzene series freeffrfom. water-solubilizing. groups, and

I OH is in one of the positions 2, ,9, andlO.

3. A compound represented byv the formula of claim 1 in whichRisav radical of thediphenyl series. free from water-solubilizing groups, and theOI-I isinone of. the.positions,2,,c9, and.10.

4. A compound representedby theformula of claim 1 in which Ris a. radical of the benzene series. free from. water-solubilizing groups, and OH. is in position. 2.

5. A compound represented by theformulaof claim 1 in which Ris aradicalof the diphenyl series free from, water-solubilizing groups, and OH isrin. position 2. 5

6. The: compound represented by the formula of claim l in which R is the radicalof 59nitro-2- amino-anisole, andQI-I is in. position 2.

7. The compoundv represented. by the'formula of, claim 1 in which R; is the. radical of 5-nitro-2- amino-toluene, and-OH is imposition 2.

8; The compound: represented by the formula of claim 1 in whichR is theradical-of dianisidine and OH- isin position. 2.

JOSEPH H. TREPAGNIER.

Patent No. 2,373,926.

It is hereby ce numbered patent r 24 incluswe, claim and that the s same may co [emu] v rtified that error appe nform to Signed and sealed Certificate of Correction I quiring corr strike out aid Letters Patent the recor this 26th day of ection as should be re June,

d of the casein JOSEPH H. TREPAGNIER ars in the prin follows: Page 2, the formula and insert inst ad Wi LESLIE FRAZER,

April 17, 1945.

the above ted specification of second column, lines ead the following th this correction therein that the the Patent ()flice.

Acting Commissioner of Patents. 

